A waterfront town with a pier, dock, and several buildings.

Chestertown Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Chestertown vacation rentals

Cabin, 1 Bedroom, Non Smoking, Lake View | Egyptian cotton sheets, premium bedding, iron/ironing board, WiFi (free)

1. Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.6 out of 10, Exceptional, (25 reviews)
"It was a great place, clean rooms, nice environment, cabins, family friendly, right on lake"
United States
Matthew
The price is ₩188,275
₩244,378 total
includes taxes & fees
Sep 8 - Sep 9
Trout House Village Resort
Apartment (0 Bedroom) | Interior

2. Schroon Lake Room < 1 Mi to Marina & Beach!

Schroon Lake Room < 1 Mi to Marina & Beach!
3.0 star property
Schroon Lake
10.0 out of 10, Exceptional, (1 review)
"Clean, comfortable room. Very friendly and welcoming hosts."
United States
Kevin
The price is ₩195,364
₩240,326 total
includes taxes & fees
Aug 17 - Aug 18
Schroon Lake Room < 1 Mi to Marina & Beach!
Apartment (0 Bedroom) | Interior

3. Cozy Room Near Schroon Lake Marina, Town & Beach!

Cozy Room Near Schroon Lake Marina, Town & Beach!
3.0 star property
Schroon Lake
6.0 out of 10, (2 reviews)
"Help!! We didn’t stay at this property due to the property stating it was lakefront and marina. The property was in complete disrepair condition. Junk cars, high weeds, room smelled of smoke. I would request a refund."
United States
Pamela
The price is ₩195,364
₩240,326 total
includes taxes & fees
Aug 16 - Aug 17
Cozy Room Near Schroon Lake Marina, Town & Beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George

8/10 Good
"Convenient location within walking distance to several local attractions"
Christine 1-night trip
Posted 2 hours ago
Howard Johnson by Wyndham Lake George

Find out more about Chestertown

Search for Vacation rentals in Chestertown on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Chestertown using one of the methods below:

  • View our selection of featured Vacation rentals in Chestertown
  • Use the map to find apartments and other Vacation homes in the Chestertown neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Chestertown while they last

Look no further and take a look at our great range of rental properties in Chestertown!

Frequently asked questions

Can I find vacation rentals in Chestertown?

Yes, we give you a choice of vacation rentals near well known points of interest in Chestertown, or you can choose a more remote option if you want a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffeehouses and forests during your trip.

How many vacation rentals will I find in Chestertown?

With 61 Expedia vacation rentals, you're sure to find just the right place for your Chestertown stay.

What’s there to see and do in Chestertown?

Friends Lake and Loon Lake are a couple of lovely local spots to get outside and enjoy nature. Hudson River and Loon Lake Beach are other places to visit while you're in town.

What’s a vacation rental in Chestertown like?

Vacation rentals are private properties you can book for a couple of days or more in Chestertown. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.